Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C305/00—Esters of sulfuric acids

Definitions

• This invention relates to a process for the direct sulfation of mixtures of primary alcohol polyethers and secondary alcohols or secondary alcohol polyethers with chlorosulfonic acid. It also relates to a method of producing mixtures of primary alcohol polyethers and secondary alcohol polyethers and the product.
• Another object of the present invention is the development of a process of direct sulfation which comprises the steps of reacting a mixture of (1) from about 0.15 to about 0.9 mol equivalents of an alcohol selected from the group consisting of a polyethyleneglycol alkyl ether of the formula wherein R represents a member selected from the group consisting of alkyl having from 5 to 19 carbon atoms, alkenyl having from 5 to 19 carbon atoms, and hydroxyalkyl having from 5 to 19 carbon atoms and n represents an interger of from 2 to 17 and a polyethyleneglycol alkylaryl ether of the formula bon atoms and the total of the carbon atoms in R and R is from 5 to 19', and secondary alcohol ethoxylates of the formula wherein R and R are alkyl havingfrom 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, and yis an integer of from 0 to 20, with from about 0.9 to about 1.25 mol equivalents per hydroxy
• a further object of the invention is the development of a process for the production of a mixture of sulfated alcohols having a sulfation degree of at least 80% which consists of the steps of reacting from about 0.9 to about 1.25 mol equivalents per hydroxyl group of anhydrous chlorosulfonic acid with a mixture of (1) from about 0.15 to about 0.9 mol equivalents of a polyethylene glycol alkyl ether of the formula wherein x represents an integer of from 4 to 18 and n represents an integer of from 2 to 17 and (2) from about 0.1 to 0.85 mol equivalents of a secondary alcohol ethoxylate of the formula CHa-(CHg)...0H(GH.).-CH.
• n O(CH CH2O)nH wherein m is an integer of from O to 17, 0 is an integer of from 0 to 17 and the sum of m -l-o is an integer of from 3 to 17, and n is an integer of from 2 to 17, at a temperature of from about 0 C.
• a yet further object of the invention is the development of a process for the production of a mixture of primary alcohol polyethers and secondary alcohol polyethers containing unreacted alcohols which comprises the steps of reacting one mol of a mixture of (1) from about 0.15 to about 0.9 mol equivalents of a primary alcohol of the formula wherein R represents a member selected from the group consisting of alkyl having from to 19 carbon atoms, alkenyl having from 5 to 19 carbon atoms, and hydroxyalkyl having from 5 to 19 carbon atoms, and (2) from about 0.1 to 0.85 mol equivalents of a secondary alkanol of the formula Ii -C Ill-R:
• R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, with from 2 to 17 mols of ethylene oxide in the presence of an acidic catalyst at a temperature below ambient temperature, and recovering a mixture of primary alcohol polyethers and secondary alcohol polyethers containing unreacted alcohols.
• secondary alcohols and secondary alcohol ethoxylates may be sulfated directly utilizing chlorosulfonic acid when the reaction is conducted in the presence of a primary alcohol ethoxylate or an alkylaryl ethoxylate.
• No solvent is required in the reaction, although a solvent can be employed if desired.
• the product of the reaction after neutralization is a mixture of sulfates of the primary alcohol ethoxylates and the secondary alcohol or secondary alcohol ethoxylates. Both of the sulfatescontribute to the surface activity of the mixture and the mixture is useful primarily as a detergent.
• the presence of the straight chain secondary alcohol ethoxylate sulfate does not impair the biodegradability of the product and greatly decreases the time required for the mixture to become degraded through biological activity.
• the presenceof the primary alcohol ethoxylate in the sulfation mixture is critical for the progress of the sulfation reaction.
• a range of from about to 90 mol percent or higher of primary alcohol ethoxylate may be employed.
• the ratio of primary alcohol ethoxylate to secondary alcohol and/or secondary alcohol ethoxylate may be varied depending on the type of final mixture of sulfated alcohols desired within the above range.
• the primary alcohol ethoxylate is preferably a polyethyleneglycol alkyl ether of the formula wherein R represents a member selected from the group consisting of alkyl having from 5 to 19 carbon atoms, alkenyl having from 5 to 19 carbon atoms, and hydroxyalkyl having from 5 to 19 carbon atoms, and n represents an integer of from 2 to 14. It is advantageous to have the recurrent CH2CH2-O units represent from about 15 to 90% of the total weight of the primary alcohol ethoxylate molecule or for n to have an average value of from about 3 to about 10.
• primary alcohol ethoxylates which contain mixtures of higher alkanols of varying chain lengths which can be from natural sources such as the fatty alcohols or from synthetic sources as obtained from petroleum.
• the primary alcohol ethoxylates may be straight chain or branched chain.
• alkylphenol ethoxylates or alkylnaphthol ethoxylates may be employed.
• the various primary alcohol ethoxylates which are utilizable in the process are the primary higher alkanol ethoxylates such as the commercial products Alfonic 1014-4 (a mixture of C to C alcohols derived from petroleum containing 40% polyoxyethylene content or an average of 3 polyoxyethylene units); Alfonic 810-6 (a mixture of C to C synthetic aliphatic alcohols containing 60% polyoxyethylene content or an average of 5.5 polyoxyethylene units); Alfonic 1012-6 (a mixture of C to C synthetic aliphatic alcohols con taining 60% polyoxyethylene content or an average of 5.25 polyoxyethylene units); a laurryl alcohol ethoxylated with about 3 polyoxyethylene units; polyethylene glycol alkenyl ethers, such as oleylpolyoxyethyl alcohol having about 5 polyoxyethylene units; and polyoxyethyleneglycol hydroxyalkyl ethers, such as l2-hydroxy-octadecylpolyoxyethyl alcohol having about 6 polyoxyethylene units
• alkylphenol ethoxylates and alkylnaphthol ethoxylates are alkylphenol ethoxylate having an average of 4 polyoxyethylene units and an average of 9 carbon atoms in the alkyl portion of the molecule.
• the secondary alcohols are those having the formula wherein R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, and preferably those having the formula g the above secondary alcohols such as a straight chain secondary alcohol ethoxylate having from 11 to 15 carbon atoms in the alcohol moiety with an average of 4 polyoxyethylene units, and Tergitol 15454, a straight chain secondary alcohol ethoxylate having from 11 to 15 carbon atoms in the alcohol moiety with an average of 3 polyoxyethylene units.
• ethoxyla-ted mixtures of primary and secondary alcohols may also be employed advantageously.
• These ethoxylated mixtures can be utilized as prepared without separation of the ethoxylation by-products (polyglycols and unreacted alcohols) as the by-produc-ts also undergo sulfation and are valuable components in the final product.
• These ethoxylated mixtures have a considerable advantage over the use of physical mixtures of primary alcohol ethoxylates with secondary alcohols and/ or secondary alcohol ethoxylates in the sulfation reaction since they are inherently less expensive to produce.
• the sulfation reaction is conducted by gradually adding chlorosulfonic acid to the mixture of alcohols while agitating and cooling to maintain the temperature between about 0 C. and C. From about 0.9 to about 1.25 mols of chlorosulfonic acid are employed per mol equivalent of hydroxyl groups present in the mixed alcohols.
• the reaction is preferably conducted while passing air or other inert gas therethrough in order to remove the HCl formed by the reaction.
• the reaction is advantageously carried out by continuous methods, introducing metered amounts of the alcohol mixture and the chlorosulfonic acid into a cooled reactor.
• the reaction must be conducted over a period of time of from 5 to 60 minutes, depending on the rate of addition of the chlorosulfonic acid and the rate of cooling of the reaction mass.
• the temperature of the reaction is preferably maintained below 50 C. As the temperature of the reaction increases substantially above about 35 C., some by-prodnets are formed decreasing the degree of sulfation of the mixed alcohols. If local overheating is avoided, temperatures up to the upper limit or higher can be employed without substantially lowering the reaction yield. At lower tempera-tures, the time of reaction is longer.
• the reaction is finished by neutralization of the reaction mixture with an aqueous or an aqueous lower alkanolic solution of an alkalizing agent selected from the group consisting of ammonia, alkali metal hydroxides and amines.
• an alkalizing agent selected from the group consisting of ammonia, alkali metal hydroxides and amines.
• neutralization is made with ammonia in a concentrated aqueous ethanolic solution (20% to 50% solution of about equal amounts of water and ethanol) or a concentrated sodium hydroxide solution (20% to 50% aqueous solution).
• a lower alkyl amine such as methylamine, trime-thylamine, ethylamine, diethylamine and triethylamine or a polyamine, such as diethylene triamine and ethylene diamine
• alkanol amines and alkanol polyamines such as diethanolamine, triethanolamine, ethoxylated amines, propyloxylated amines, ethoxylated polyamines, etc.
• reaction mixture after neutralization may be employed as such for detergent usages without other separation steps.
• the products of the reaction contain at least 80% of starting alcohol groups in the form of sulfates. Degrees of sulfation of 95% or higher are readily obtained.
• direct sulfation of secondary alcohols with chlorosulfonic acid it is impossible to obtain commercially acceptable products with a degree of sulfation of over 80% and direct sulfation of secondary alcohol ethoxylates with chlorosulfonic acid can only be conducted at very low temperatures, C. or less, over long periods of time, to give products having sulfation degrees in excess of 80%.
• the ethoxylated mixtures of primary and secondary alcohols are prepared by reacting from about 2 to about 17 mols of ethylene oxide with about one mol of a mixture of (1) from about 0.15 to about 0.9 mol equivalents of a primary alkanol having from 6 to 20 carbon atoms and (2) from about 0.1 to about 0.85 mol equivalents of a secondary alkanol of the formula wherein R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, under the customary ethoxylation conditions and recovering the ethoxylated mixture by customary procedures.
• the reaction is conducted under the customary ethoxylation conditions as known in the art, utilizing ethoxylation catalysts and ethoxylation temperatures.
• an acidic ethoxylation catalyst such as boron trifluoride or its complexes at temperatures below the ambient temperature and preferably at temperatures between about 5 C. and 15 C., the ethoxylation reaction continued to substantial completion when mixed alcohols were employed.
• R represents a member selected from the group consisting of alkyl having from 5 to 19 carbon atoms, alkenyl having from 5 to 19 carbon atoms, and hydroxyalkyl having from 5 to 19 carbon atoms.
• Any primary alkanol containing from 6 to 20 carbon atoms may be employed. These can be either straight or branched chain in the alkyl portion although the straight chain alkanols are preferable from the viewpoint of biodegradability of the final sulfated product.
• the primary alkanols can also be derived by synthesis and can be a mixture of alkanols as obtained from the hydrogenation of natural fats or from synthetic processes.
• Such primary alkanols are Alfol ClO-Cl4 (a mixture of C to C primary alkanols derived from petroleum), lauryl alcohol, stearyl alcohol, coconut fatty alcohols derived by the hydrogenation of coconut oil, etc. It is also possible to utilize unsaturated and hydroxylated primary alcohols such as oleyl alcohol and 12-hydroxy-octadecyl alcohol.
• the resulting mixture contains about 0.5% to 1% of polyglycols and from about 10% to 20% of unreacted alcohols.
• this mixture is sulfated according to the invention, extremely stable sulfated products are obtained which do not undergo detectable hydrolysis even when solutions of the same were subjected to temperatures of 60 C. for several weeks.
• Example I 165 gm. (0.5 mols) of a primary alcohol ethoxylate containing from 10 to 14 carbon atoms in the alcohol moiety and an average of 3 oxyethylene units (Alfonic 10144) (M.W. 330) and gm. (0.5 mol) of a secondary straight chain aliphatic alcohol having from 10 to 13 carbon atoms and an average molecular weight of 190 were mixed together.
• gm. (about 1.03 mols) of anhydrous chlorosulfonic acid were gradual- 1y added while agitating the mixture and passing air therethrough. The reaction temperature was maintained at from 20 C. to 25 C. by cooling. On completion of the addition of the chlorosulfonic acid, a dark amber viscous liquid was formed.
• reaction product was then neutralized by a mixture consisting of 95 gm. of 28% aqueous ammonia solution, 60 gm. of ethyl alcohol and 90 gm. of water. A yellow, free-flowing liquid was obtained.
• This product consisted of 53.5% alcohol sulfates and 4.3% unsulfated alcohols.
• the starting alcohols were 90.0% sulfated (90.0% sulfation degree).
• a 10% solution of the product had a pH of 7.4.
• Example II Example I was repeated except that gm. 1.11 mols) of chlorosulfonic acid were utilized. The reaction conditions were maintained the same.
• the starting alcohols were 94.7% sulfated.
• Example III 110 gm. (0.33 mol) of Alfouic 1014-4 and 130 gm. (0.67 mol) of a secondary straight chain aliphatic alcohol having from 10 to 13 carbon atoms and an average molecular weight of 190 were mixed together.
• 130 gm. (about 1.11 mols) of anhydrous chlorosulfonic acid were gradually added under the same conditions as in Example I, except the reaction temperature was maintained at 25 C. to 35 C.
• the starting alcohols were 87.2% sulfated.
• Example IV Alcohol sulfates "percent" 46.9 Unsulfated alcohols percent 7.3 pH10% solution 7.0 The starting alcohols were 81.8% sulfated.
• Example V 33 gm. (0.1 mol) of Alfonic 1014-4 and 172 gm. (0.9 mol) of a secondary straight chain aliphatic alcohol having from 10 to 13 carbon atoms and an average molecular weight of 190 were mixed together. To this mixture, 130 gm. (about 1.11 mols) of anhydrous chlorosulfnic acid were gradually added under the same conditions as in Example I.
• the reaction product wa neutralized by a mixture of 100 gm. of a 50% NaOH solution and 500 gm. of water. After neutralization, a cloudy material was obtained which separated on standing. The product obtained had a sulfation degree of 60.4%.
• This example demonstrates the criticality of maintaining at least a 0.15 mol amount of primary alcohol ethoxylate in the sulfation mixture.
• Example VI 164.5 gm. (0.5 mol) of Alfonlc 1014-4 and 93 gm.
• reaction product was neutralized with a mixture of 100 gm. of 28% aqueous ammonia, 60 gm. of ethyl alcohol and 55 gm. of water. After neutralization a yellow, free-flowing liquid was obtained which had the following analysis:
• the starting alcohols were 88.7% sulfated.
• Example VII 164.5 gm. (0.5 mol) of Alfonic 1014-4 and 72 gm. (0.5 mol) of di-isobutyl carbinol having the formula were mixed together. To this mixture 130 gm. (about 1.11 mols) of anhydrous chlorosulfonic acid were gradually added under the same conditions as in Example I, except that the reaction temperature wa maintained between 17 C. and 22 C.
• the reaction product was neutralized with a mixture of 100 gm. of 28% aqueous ammonia, gm. of ethyl alcohol and 55 gm. of water. After neutralization a clear, free-flowing yellow liquid was obtained having the following analysis:
• Example VIII 165 gm. (0.5 mol) of a primary alcohol ethoxylate containing from 10 to 14 carbon atoms in the alcohol moiety and an average of 3 oxyethylene units (Alfonic 1014-4) (M.W. 330) and 172 gm. (0.5 mol) of a secondary straight chain alcohol ethoxylate containing from 10 to 13 carbon atoms in the aliphatic carbon chain of the alcohol moiety and an average of 3.5 oxyethylene units (M.W. 344) were mixed together. To this mixture 130 gm. (about 1.11 mols) of anhydrous chlorosulfonic acid were gradually added while agitating the mixture and passing air therethrough. The reaction temperature was maintained at from 15 C. to 20 C. on cooling. On completion of the addition of the chlorosulfonic acid, a dark amber, viscous product was formed.
• reaction product was then neutralized by a mixture consisting of about 100 parts of 28% aqueous ammonia solution, 55 parts ethyl alcohol and parts of Water. A light yellow, free-flowing liquid was obtained.
• the product analyzed 60.7% alcohol sulfates and 2.9% unsulfated alcohols.
• the starting alcohols were 94.3% sulfated (94.3% sulfation degree).
• a 10% solution of the product had a pH of 7.3.
• Example IX To determine the effect of the temperature of the reaction, 0.25 mol of a primary alcohol ethoxylate Alfonic 1014-4 and 0.25 mol of a secondary straight chain alcohol ethoxylate containing from 10 to 13 carbon atoms in the aliphatic carbon chain of the alcohol moiety and an average of 3 oxyethylene units were mixed together and reacted with gm. (0.55 mol) of anhydrous chlorosulfonic acid while agitating thoroughly and passing air therethrough.
• reaction mixtures were neutralized with a mixture of 45 gm. of a 28% aqueous ammonia solution,
• the reaction product was neutralized with a mixture oi 104 gm. of a 28% aqueous ammonia solution, 90 gm. of ethyl alcohol and 90 gm. of water. A golden yellow, free-flowing liquid was obtained.
• the product had the following analysis:
• Example XII Example VIII was repeated using 0.5 mol of a natural lauryl alcohol, Lorol 5, ethoxylated with an average of 3 oxyethylene units as the primary alcohol ethoxylate.
• the sulfated product was neutralized with a mixture consisting of 100 gm. of 28% aqueous ammonia solution, 70 gm. of ethyl alcohol and 70 gm. of water.
• a yellow, free-flowing liquid was otbained with the following analys1s:
• Example XIII 218 gm. (0.5 mol) of Sterox, an alkylphenol ethoxylate having an average of 4 polyoxyethylene units and an average of 9 carbon atoms in the alkyl portion of the molecule, and 0.5 mol of a secondary straight chain alcohol ethoxylate containing 12 to 15 carbon atoms and 3 oxyethylene units were mixed together.
• 130 gm. (about 1.11 mols) of anhydrous chlorosulfonic acid were gradually added under the same conditions as in Example VIII, except that the reaction temperature was maintained between 18 C. and 21 C.
• reaction product was neutralized with a mixture consisting of 100 gm. of 28% aqueous ammonia, 75 gm. of ethyl alcohol and 75 gm. of water. After neutralization a yellow, free-flowing liquid was obtained having the following analysis:
• Example XIV A mixture of 154.5 gm. (0.5 mol) of a secondary straight chain alcohol ethoxylate containing 10 to 13 carbon atoms and 3 oxyethylene units, 164.5 gm. (0.5 mol) of Alfonic 1014-4 and 37 gm. of diethylether were reacted with 130 gm. (1.11 mole) of anhydrous chlorosulfonic acid at a temperature of 8 C. to 11 C. under the conditions of Example VIII. The sulfated mixture was neutralized with a mixture of 100 gm. of a 50% NaOH solution and 800 gm. of water and the diethylether was removed by distillation. A pale yellow liquid remained which analyzed:
• Example XV A mixture of 0.5 mol of Alfonic 1014-4, 0.5 mol of a secondary straight chain alcohol ethoxylate containing 12 to 15 carbon atoms and 3 oxyethylene units and 100 gm. (0.25 mol) of a polyoxyethylene glycol having an average molecular weight of 400 were reacted with 1.1 mols of anhydrous chlorosulfonic acid at a temperature of 12 C. to 17 C. under the conditions of Example VIII. The sulfated mixture was neutralized with a mixture of 100 gm. of 28% aqueous ammonia solution, gm. of ethyl alcohol and 70 gm. of water. A yellow, freefiowing liquid was obtained which analyzed:
• Example XVI 132 gm. (0.4 mol) of Alfonic 1014-4 and 180 gm. (0.4 mol) of a branched chain secondary alcohol ethoxylate of 2,6,8-trimethyl-4-nonanol having an average of 6 oxyethylene units (Tergitol TMN) were mixed together.
• 103 gm. (about 0.88 mol) of anhydrous chlorosulfonic :acid were gradually added under the same conditions as in Example VIII, except that the reaction temperature, was maintained between 17 C. and 21 C.
• reaction product was neutralized with a mixture of gm. of 28% aqueous ammonia, 65 gm. of ethyl alcohol and 50 gm. of water. After neutralization a yellow, free-flowing liquid was obtained which had the following analysis:
• the reaction product was neutralized with a mixture of gm. of a 28% aqueous ammonia solution, 70 gm. of ethyl alcohol and 70 gm. of water. A yellow, freeflowing liquid was obtained.
• the product had the following analysis:
• Example XVIII 161.5 gm. (0.5 mol) of Lipal 3T-D and 95.5 gm. (0.5 mol) of a secondary straight chain aliphatic alcohol having from 10 to 13 carbon atoms and an average molecular weight of 190 were mixed together.
• 130 gm. (about 1.11 mols) of anhydrous chlorosulfonic acid were gradually added while agitating the mixture and passing air therethrough.
• the reaction temperature was maintained at from C. to C. by cooling.
• reaction product was then neutralized by a mixture consisting of 100 gm. of 28% aqueous ammonia solution, 60 gm. of ethyl alcohol and 60 gm. of water. A yellow, free-flowing liquid was obtained.
• This product consisted of 54.4% alcohol sulfates and 2.8% unsulfated alcohols.
• the starting alcohols were 93.3% sulfated (93.3% sulfation degree).
• a 10% solution of the product had a pH of 8.3.
• Example XIX.Ethoxylation of mixed alcohols 1 mol of a commercial secondary alkanol having from 12 to 15 carbon atoms and an average molecular weight of 201 and 1 mol of a commercial primary fatty alcohol having from 10 to 14 carbon atoms and an average molecular weight of 183 were mixed, then ethoxylated using boron trifluoride as a catalyst. The temperature was maintained at from 5 C. to 15 C. during the ethoxylation and 3 mols of ethylene oxide were added per mol equivalent of the alcohol mixture. The unreacted alcohol was not removed from the ethoxylation mixture.
• the mixed ethoxylated product was a colorless material having the following analysis:
• Example XX 2 mol equivalents of the mixed ethoxylated alcohols of Example XIX (as determined by the Hydroxyl Number) were placed in the reaction vessel. 2.06 mols of anhydrous chlorosulfonic acid were gradually added while agitating the mixture and passing air therethrough. The reaction temperature was maintained at from 20 C. to C. by cooling.
• the reaction product was split in half and each moiety was neutralized.
• the first moiety was neutralized by a mixture consisting of 95 gm. of 28% aqueous ammonia solution, 60 gm. of ethyl alcohol and 90 gm. of water. A clear yellow liquid was obtained containing approximately 60% alcohol sulfates.
• the second moiety was neutralized by a mixture of 100 gm. of a NaOH solution and 500 gm. of water. A clear yellow liquid was obtained containing approximately 40% alcohol sulfates.
• the mixed alcohol ether sulfates of the invention without having removed the unethoxylated primary and secondary alcohols after sulfation, produced very stable compounds. Stability tests were run at room temperature and at the temperature of 60 C. for several weeks. No change in pH was observed in spite of the presence of unethoxylated secondary alcohol sulfates, which are known to hydroylze very easily on standing at room temperature.
• a process of direct sulfation which comprises the steps of reacting a mixture of (1) from about 0.15 to about 0.9 mol equivalents of an alcohol selected from the group consisting of a polyethylene glycol alkyl ether of the formula wherein R represents a member selected from the group consisting of alkyl having from 5 to 19 carbon atoms, alkenyl having from 5 to 19 carbon atoms, and hydroxyalkyl having from 5 to 19 carbon atoms and n represents an integer of from 2 to 17 and a polyethylene glycol alkylaryl ether of the formula wherein R represents alkylaryl having from 7 to 24 carbon atoms and n represents an integer from 2 to 17, and (2) from about 0.1 to 0.85 mol equivalents of an alcohol selected from the group consisting of alcohols of the formula wherein R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, and secondary alcohol ethoxylates of the formula wherein R and R are alkyl having from
• sulfated alcohols having a sulfation degree of at least 2.
• a process for the production of a mixture of sulfonated alcohols having a sulfation degree of at least 80% which consists of the steps of reacting from about 0.9 to about 1.25 mol equivalents per hydroxyl group of anhydrous chlorosulfonic acid with a mixture of (1) from about 0.15 to about 0.9 mol equivalents of a polyethylene glycol alkyl ether of the formula.
• x represents an integer of from 4 to 18 and n represents an integer of from 2 to 17 and (2) from about 0.1 to 0.85 mol equivalents of a secondary alcohol ethoxylate of the formula wherein m is an integer of from to 15, 0 is an integer of from 0 to 15 and the sum of m+0 is an integer of from 5 to 15, and n is an integer of from 2 to 17, at a temperature of from about 0 C.
• a process for the production of a mixture of sulfated alcohols having a sulfation degree of at least 80% which consists of the steps of reacting from about 0.9 to about 1.25 mol equivalents per hydroxyl group of anhydrous chlorosulfonic acid with a mixture of (1) from about 0.15 to about 0.9 mol equivalents of a polyethylene glycol alkylaryl ether of the formula wherein R represents alkylaryl having from 7 to 24 carbon atoms and n represents an integer from 2 to 17, and (2) from about 0.1 to 0.85 mol equivalents of an alcohol selected from the group consisting of alcohols of the formula wherein R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, and secondary alcohol ethoxylates of the formula Rr-CHR2 O(CH CH2O) OH CH2-OH wherein R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R
• alkali metal hydroxides alkyl amines, polyamines, alkanol amines, and alkanol polyamines, and recovering neutralized mixed sulfated alcohols having a sulfation degree of at least 80%.
• a process for the production of a mixture of sulfated alcohols having a sulfation degree of at least 80% which consists of the steps of reacting from about 0.9 to about 1.25 mol equivalents per hydroxyl group of anhydrous chlorosulfonic acid with a mixture of (1) from about 0.15 to about 0.9 mol equivalents of a polyethylene glycol alkyl ether of the formula wherein x represents an integer of from 4 to 18 and n represents an integer of from 2 to 17, and (2) from about 0.1 to 0.85 mol equivalents of an alcohol selected from the group consisting of alcohols of the formula wherein R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, and secondary alcohol ethoxylates of the formula wherein R and R are alkyl having from 1 to 18 carbon atoms and the total of the carbon atoms in R and R is from 5 to 19, and y is an integer of from 0 to 20, at a temperature of from

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